Matrix model to predict specific optical rotations of acyclic chiral molecules

Tetrahedron

Volumn 63, Issue 10, 2007, Pages 2292-2314

  Zhu, Hua Jie ^a   Ren, Jie ^a   Pittman Jr , Charles U ^b  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

B3LYP; Determinant; Matrix; Optical rotation

Indexed keywords

ALCOHOL; AMINOALCOHOL; CYANOHYDRIN; CYSTEINE; EPHEDRINE; PSEUDOEPHEDRINE;

ARTICLE; CALCULATION; GEOMETRY; MAGNITUDE ESTIMATION METHOD; MATHEMATICAL MODEL; OPTICAL ROTATION; PREDICTION; PRIORITY JOURNAL;

EID: 33846585388     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.061     Document Type: Article

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173. Generally, the van der Waal's radius of any atom is about 0.8 Å larger than the same atom's valence radius. We use the average value 0.8 Å as the plus value in the calculation of radius of the substituents.
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175. Chiral Nonracemic Compounds (1998-1999), Aldrich p 35
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177. Pickard R.H., and Kenyon J. J. Chem. Soc. 103 (1913) 1923
178. Chiral Nonracemic Compounds (1998-1999), Aldrich p 150
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182. Chiral Nonracemic Compounds (1998-1999), Aldrich p 104
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188. Chiral Nonracemic Compounds (1998-1999), Aldrich p 106
189. Beilstein 1, 202 for (S)-configuration;
190. Lowry T.M., and Dickson T.W. J. Chem. Soc. 103 (1913) 1076
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195. Chiral Nonracemic Compounds (1998-1999), Aldrich p 41
196. Beilstein 4, 160;
197. Warren Jr. M.E., and Smith H.E. J. Am. Chem. Soc. 87 (1965) 1757
198. Chiral Nonracemic Compounds (1998-1999), Aldrich p 60
199. Beilstein 12, 95;
200. Chiral Nonracemic Compounds (1998-1999), Aldrich p 226
201. Chiral Nonracemic Compounds (1998-1999), Aldrich p 131
202. Beilstein 12, 1092;
203. Chiral Nonracemic Compounds (1998-1999), Aldrich p 138
204. D is +41.3 (EtOH) in the reference of. Collyer T.A., and Kenyon J. J. Chem. Soc. (1940) 676
205. Soai K., Ookawa A., Kaba T., and Ogawa K. J. Am. Chem. Soc. 109 (1987) 7111
206. Chiral Nonracemic Compounds (1998-1999), Aldrich p 139
207. See Ref. 33p;
208. Levenem P.A., and Mikeska L.A. J. Biol. Chem. 75 (1927) 598
209. Chiral Nonracemic Compounds (1998-1999), Aldrich p 142
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211. Chiral Nonracemic Compounds (1998-1999), Aldrich p 79
212. Snyder H.R., and Brewster J.H. J. Am. Chem. Soc. 71 (1949) 291 reported the rotation data
213. A subsequent report mentioned that the data were not optical rotation values:. Snyder H.R., and Brewster J.H. J. Am. Chem. Soc. 71 (1949) 4165
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216. Soai K., and Yokoyama. J. Chem. Soc., Chem. Commun. (1987) 1690
217. Beilstein 6, 3041;
218. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 108 (1986) 6071
219. See Ref. 33g;
220. Chiral Nonracemic Compounds (1998-1999), Aldrich p 125
221. Chiral Nonracemic Compounds (1998-1999), Aldrich p 53
222. Chiral Nonracemic Compounds (1998-1999), Aldrich p 137
223. Vignerou J.P., and Jacquet I. Tetrahedron 32 (1976) 939
224. Yamaguchi S., and Mosher H.S. J. Org. Chem. 38 (1973) 1870
225. Chiral Nonracemic Compounds (1998-1999), Aldrich p 54
226. Oeveren A.V., Menge W., and Feringa B.L. Tetrahedron Lett. 30 (1989) 6427
227. Noyori R., Tomino I., Tanimoto Y., and Nishizaawa M. J. Am. Chem. Soc. 106 (1984) 6717
228. Chiral Nonracemic Compounds (1998-1999), Aldrich p 130
229. Chiral Nonracemic Compounds (1998-1999), Aldrich p 1
230. See Ref. 9e;
231. See Ref. 33ah;
232. Beilstein 1, 1440;
233. Chiral Nonracemic Compounds (1998-1999), Aldrich p 33
234. Beilstein 1, 136;
235. See Ref. 33ao;
236. Chiral Nonracemic Compounds (1998-1999), Aldrich p 44
237. Beilstein 1, 2218;
238. See Ref. 33al;
239. Chiral Nonracemic Compounds (1998-1999), Aldrich p 52
240. Goering H.L., Briody R.G., and Sandrock G. J. Am. Chem. Soc. 92 (1970) 7401
241. Chiral Nonracemic Compounds (1998-1999), Aldrich p 120
242. Beilstein 3, 447;
243. Chiral Nonracemic Compounds (1998-1999), Aldrich p 14
244. Beilstein 4, 735;
245. Chiral Nonracemic Compounds (1998-1999), Aldrich p 122
246. Beilstein 4, 298;
247. Chiral Nonracemic Compounds (1998-1999), Aldrich p 159
248. Beilstein 1, 472;
249. See Ref. 33al;
250. Beilstein 3, 279;
251. Chiral Nonracemic Compounds (1998-1999), Aldrich p 2
252. Beilstein 3, 189;
253. See Ref. 33ae;
254. Beilstein 10, 195;
255. See Ref. 33p;
256. Chiral Nonracemic Compounds (1998-1999), Aldrich p 115
257. Beilstein 1, 138;
258. Chiral Nonracemic Compounds (1998-1999), Aldrich p 133
259. Beilstein 2, 248;
260. Chiral Nonracemic Compounds (1998-1999), Aldrich p 152
261. Beilstein 6, 5939;
262. See Ref. 33aw;
263. Chiral Nonracemic Compounds (1998-1999), Aldrich p 140
264. Beilstein 21, 217;
265. Chiral Nonracemic Compounds (1998-1999), Aldrich p 76
266. Beilstein 4, 1666;
267. Chiral Nonracemic Compounds (1998-1999), Aldrich p 155
268. Chiral Nonracemic Compounds (1998-1999), Aldrich p 154
269. Beilstein 14, 1188;
270. Chiral Nonracemic Compounds (1998-1999), Aldrich p 6
271. Beilstein 4, 2485;
272. See Ref. 33o;
273. Beilstein 2, 863;
274. Chiral Nonracemic Compounds (1998-1999), Aldrich p 13
275. Chiral Nonracemic Compounds (1998-1999), Aldrich p 153
276. Beilstein 8, 167;
277. Chiral Nonracemic Compounds (1998-1999), Aldrich p 20
278. Beilstein 8, 167;
279. Chiral Nonracemic Compounds (1998-1999), Aldrich p 11
280. See Ref. 33av;
281. See Ref. 33aaq;
282. Chiral Nonracemic Compounds (1998-1999), Aldrich p 86
283. Beilstein 1, 1567;
284. Chiral Nonracemic Compounds (1998-1999), Aldrich p 168
285. Beilstein 3, 481;
286. See Ref. 33b;
287. See Ref. 33aat;
288. Beilstein 13, 636;
289. Chiral Nonracemic Compounds (1998-1999), Aldrich p 160
290. 0 value induced by a specific solvent tends to be a constant value for very similar chiral molecules.
291. Aldrich Handbook of Fine Chemicals and Laboratory Equipment (2000-2001), Sigma-Aldrich, Milwaukee, WI The rotation data are collected from the pp 484-485
292. 3 is collected from the Ref. 32.
293. 3 is collected from. Wells P.R. Prog. Phys. Org. Chem. 6 (1968) 111
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